1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 60134427, compound

HRID 2061030Notes

Reaction equation

HRID 2061030 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:18])([CH3:17])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.C(N(CC)C(C)C)(C)C.[CH3:40][NH:41][CH2:42][CH2:43][N:44]([CH3:46])[CH3:45]>CN(C)C=O.O>[CH3:45][N:44]([CH3:46])[CH2:43][CH2:42][N:41]([CH3:40])[C:14](=[O:16])[CH2:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 145510073-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 60134427HCID 60134427, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(benzyloxycarbonylamino)-3-methylbutanoic acid (described in international publication number WO 2008/083347 A1) (5.74 g, 22.9 mmol) in N,N-dimethylformamide (150 ml) was added N,N-carbonyldiimidazole (4.45 g, 27.4 mmol). The reaction mixture was stirred for 1 hour at room temperature. N,N-diisoproylethylamine (11.2 ml, 68.8 mmol) and N,N,N-trimethylethylenediamine (3.6 ml, 27.8 mmol) were added was added to the reaction mixture. The mixture was stirred for an additional 18 hours at room temperature. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic layer was washed two more times with water and dried over sodium sulfate. The dried organic layer was filtered and concentrated in vacuo. The crude product was purified on silica gel column chromatography (0 to 10% methanol in dichloromethane) to give 2.08 g (27% yield) of benzyl 4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methyl-4-oxobutan-2-ylcarbamate. 1H NMR (CDCl3) δ 7.34-7.26 (m, 5 H), 6.14 (s, 1 H), 5.04 (s, 2 H), 3.47 (t, J=5.3 Hz, 2 H), 3.02 (s, 3 H), 2.60 (s, 2 H), 2.59 (t, J=5.3 Hz, 2 H), 2.24 (s, 6 H), 1.46 (s, 6 H); MS (ESI+) calculated for C18H30N3O3: 335.23, Found: 336.2 (M+H+).

Workup

  1. additionwas added to the reaction mixture
  2. stirringThe mixture was stirred for an additional 18 hours at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed two more times with water
  5. dry with materialdried over sodium sulfate
  6. filtrationThe dried organic layer was filtered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7f6fa296bb344ceebbe1af91ea453cbb
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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